The Milwaukee Bucks are treading dangerous ground full of wonderful and terrifying possibilities

This looked like a summer of opportunity for the Milwaukee Bucks, and through the first few days of free agency they've worked hard (or hardly worked?) to keep their options open. Their first-round draft pick was an obvious play for the future, and now the Bucks have waved goodbye to a pair of free-agents. First Mike Dunleavy Jr. agreed to a two-year, $6 million deal with the Chicago Bulls, a smart move made with little fanfare and accompanied by many longing sighs from Bucks fans. Then Tuesday night the Bucks agreed to a three-team trade that will send J.J. Redick to the Los Angeles Clippers on a 4-year, $27 million contract. The Bucks were unable to land point guard Eric Bledsoe, a surprising and disappointing revelation for many fans who were still dreaming sweet dreams after rumors from Monday indicated trade talks were ongoing. They did receive two second-round picks (one from each team, reportedly) for facilitating the deal, however.

While both Redick and Dunleavy remain on the Bucks' ledger until the July Moratorium ends on July 9th, their eventual departure clears a little over $14 million in the form of their cap holds: approximately $9.3 million for Redick, $4.9 million for Dunleavy. While the Bucks remain over the cap due to large holds for Monta Ellis (should be $16-17m) and Samuel Dalembert (appx. $8.7m), they're much closer to having a level of financial flexibility they haven't seen in some time. It's still anybody's guess what will happen to Monta Ellis, but Dalembert is almost certainly gone, whether the Bucks simply renounce him or manage to swing another sign-and-trade.

One might assume that the possibility for big cap space and a generally apathetic front office attitude toward the early days of free agency, typically filled with the more head-scratching agreements of the offseason, would delight Bucks fans. But you would be wrong, because these are Bucks fans we're talking about for cryin' out loud. Instead, many are shifting nervously in their chairs and tugging at collars, wondering which laps all these bags of money will eventually be dumped in. And to be fair, there are reasons to be very, very afraid. The Bucks "have to" spend a certain amount of money on the roster to reach the salary floor. I use quotes because it's not like they get kicked out of the league if they don't--they simply pay the difference in equal amounts to each player on the roster, though that's not something Herb Kohl is likely to be too excited about. There's also the little matter of actually assembling a complete roster: the Bucks still have just ten players under contract (counting Antetokounmpo and Wolters) and only two of them are guards. So there are going to be some contracts coming in either via trade or free agent signings.

History doesn't lend Milwaukee much credit in that regard. Their most recent free agent frenzy netted the disastrous deals of John Salmons and Drew Gooden. The former was ditched by trading out of the lottery in the 2011 draft, the latter is a candidate to be amnestied this summer (note that such a move has to be completed within the first week after the July Moratorium ends). The Bucks' best free agency decision in recent years was arguably the Dunleavy signing, a small deal made with exception dollars that carried very little risk. The Ersan Ilyasova extension has also proven smart to date. But when it comes to long-term, big money deals, Gooden and Salmons are the two most notable pieces of John Hammond handiwork, with a third more murky instance being the reported extension offer to Monta Ellis.

This naturally has people scared of what will come next, especially as they watch many of the more acceptable targets accepts offers from other teams:

• The Timberwolves will retain G/F Chase Budinger with a 3-year, $16 million offer which includes a player option in year 2. The Bucks were reportedly going hard after Budinger and may have in fact been close to nabbing him.
• The Wolves will also sign shooting guard Kevin Martin to a 4-year, $28 million contract. Martin was reportedly one of the first players contacted by the Bucks when free agency opened. On the flip side, the move likely ends Andrei Kirilenko's tenure in Minnesota. He played well last season and could be a good fit for the Bucks on a short deal, even if the annual salary was high.
• Tony Allen, another player the Bucks reportedly had interest in, will stay with the Grizzlies on a 4-year deal.